[ CAS No. 372118-01-9 ]

Name: 372118-01-9|Methyl 4,6-dichloropyridazine-3-carboxylate|98%
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Quality Control of [ 372118-01-9 ]

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Product Details of [ 372118-01-9 ]

CAS No. :	372118-01-9	MDL No. :	MFCD09953612
Formula :	C₆H₄Cl₂N₂O₂	Boiling Point :	345.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	207.01 g/mol	Pubchem ID :	17848322
Synonyms :

Safety of [ 372118-01-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 372118-01-9 ]

Upstream synthesis route of [ 372118-01-9 ]
Downstream synthetic route of [ 372118-01-9 ]

[ 372118-01-9 ] Synthesis Path-Upstream 1~3

1
[ 372118-00-8 ]
[ 372118-01-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 95℃; for 5 h;	Step 3 4,6-Dichloro-pyridazine-3-carboxylic acid methyl ester A mixture of 4,6-dihydroxy-pyridazine-3-carboxylic acid methyl ester (10.5 g, 61.7 mmol) and POCl₃ (70 mL) was heated to 95° C. for 5 h. The excess POCl₃ was removed under reduced pressure, then the crude residue was added to ice-water (250 mL) and extracted with ethyl acetate (3*100 mL). The combined extracts were dried then concentrated to give a crude residue which was purified by chromatography (silica, 100-200 mesh, 30percent ethyl acetate in hexane) to give 4,6-dichloro-pyridazine-3-carboxylic acid methyl ester (9.2 g, 72percent) as an off white solid. LC-MS: 207.0 [M+H]⁺.

Reference： [1] Patent: US2013/178478, 2013, A1, . Location in patent: Paragraph 0301;0302
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2683 - 2691
[3] Patent: US2004/77653, 2004, A1, . Location in patent: Page 18

2
[ 1830-54-2 ]
[ 372118-01-9 ]

Reference： [1] Patent: US2013/178478, 2013, A1,
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2683 - 2691
[3] Patent: US2004/77653, 2004, A1,

3
[ 83878-89-1 ]
[ 372118-01-9 ]

Reference： [1] Patent: US2013/178478, 2013, A1,
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2683 - 2691
[3] Patent: US2004/77653, 2004, A1,

[ 372118-01-9 ] Synthesis Path-Downstream 1~25

1
[ 372118-01-9 ]
[ 124-41-4 ]
[ 679405-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; at 0 - 20℃;	Step 4.Preparation of 6-chloro-4-methoxy-pyridazine-3-carboxylic acid methyl ester 6 sodium methoxide (25 wt % I methanol, 1.1 ML) is added to a stirred solution of <strong>[372118-01-9]4,6-dichloro-pyridazine-3-carboxylic acid methyl ester</strong> (1.03 g, 5 mmol) in THF (25 ML) cooled to 0 C. The reaction mixture is stirred at room temperature overnight and then poured into 1N HCl (8 ML).The resulting solution is then neutralized by saturated NaHCO3. EtOAc (20 ML) is added and the layers are separated.The aqueous layer is extracted twice with EtOAc (20 ML) and the combined extracts are washed with brine (25 ML), dried (Na2SO4) and evaporated.The residue is then purified by flash column chromatography (silica gel, eluted with 2:1 hexane:EtOAc) to give 6-chloro-4-methoxy-pyridazine-3-carboxylic acid methyl ester as a white solid.

Reference： [1]Patent: US2004/77653,2004,A1 .Location in patent: Page 18

Yield	Reaction Conditions	Operation in experiment
		(3) A mixture of the compound (prepared in the above (2)) 8.06 g and phosphoryl chloride 80 ml is stirred at 100 C. for 4 hours. After removal of the excess phosphoryl chloride, the residue is poured into ice-water and extracted with ethyl acetate, washed with water (twice) and brine, and dried over sodium sulfate. After removal of the sodium sulfate, the filtrate is concentrated in vacuo, and the residue is purified with column chromatography (silica gel 200 g, solvent; hexane:ethyl acetate=4:1) to give 3-methoxycarbonyl-4,6-dichloropyridazine as colorless crystals 7.44 g. mp 57-59.5 C.

3
[ 372118-01-9 ]
[ 52605-49-9 ]
[ 1030382-76-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In acetonitrile; at 20 - 80℃; for 20h;	To a stirred solution of <strong>[372118-01-9]4,6-dichloro-pyridazine-3-carboxylic acid methyl ester</strong>(2.9 g, 14 mmol) and sarcosine ethyl ester hydrochloride (2.15 g, 14 mmol) in acetonitrile (75 ml) was added triethylamine (4.9 mL, 35 mmol). The resultant reaction mixture was stirred at room temperature for 2 hours before adding further triethylamine (4.9 mL, 35 mmol) and heating the reaction mixture at 80C for 18 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resultant residue treated with water and extracted with ethyl acetate (x 3), the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo to give a solid. The solid was triturated in hot methanol to give the title compound as a yellow solid (1.6 g, 45%). LCMS (method B): Rx = 2.64 min, M+H+ = 256.

Reference： [1]Patent: WO2008/67481,2008,A1 .Location in patent: Page/Page column 84

4
[ 372118-01-9 ]
[ 1040246-87-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With lithium hydroxide; In tetrahydrofuran; at 0℃; for 0.666667h;	To a solution of <strong>[372118-01-9]methyl 4,6-dichloropyridazine-3-carboxylate</strong> (5.5 g, 26.6 mmol) in THF (60 mL), at 0 C. was added 1M solution of lithium hydroxide (39.9 mL, 39.9 mmol) with stirring. The resultant mixture was stirred continuously at 0 C. for 40 min. The THF was removed and the aqueous layer was acidified with 1.5N HCl to give a white solid. The mixture was filtered and the solid filter cake was washed with water and dried under vacuum overnight to give 4,6-dichloropyridazine-3-carboxylic acid (5 g, 25.9 mmol, 98% yield). MS (M+1) m/z: 193 (MH+). LC retention time 0.19 min [D].
		[00286] Step A: Preparation of 4,6-dichloro-pyridazine-3-carboxylic acid:[00287] To a solution of methyl 4,6-dichloro-pyridazine-3-carboxylate (6.01 g, 29.03 mmol, WO 2004/031174) in THF (29 ml) at 0 C is added 29 ml of aqueous 1.0 M LiOH with stirring. The resulted mixture is stirred continuously at 0 C for 40 min and monitored by TLC. The reaction mixture is diluted with water, and acidified to pH 1-2 with aqueous 1.0 M HCl. The crude product is suspended between the organic and aqueous layers. After filtration and washed with water and hexane, and dried under vacuum, the product is obtained.
	With sodium hydroxide; In tetrahydrofuran; water; at 0℃; for 1h;	(step 1) Methyl 4,6-dichloropyridazine-3-carboxylate (100 mg, 0.483 mmol) was dissolved in THF (3 mL), and the mixture was stirred at 0C for 15 min. To the reaction mixture was added 4 mol/L aqueous sodium hydroxide solution (0.362 mL, 1.449 mmol), and the mixture was stirred at 0C for 1 hr. To the reaction mixture was added 1 mol/L hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of 4,6-dichloropyridazine-3-carboxylic acid, which was used for the next reaction without purification. ESIMS m/z: 193 (M + H)+

Reference： [1]Patent: US2019/152948,2019,A1 .Location in patent: Paragraph 0418-0419; 0414
[2]Patent: WO2008/89459,2008,A1 .Location in patent: Page/Page column 76
[3]Patent: EP2927214,2015,A1 .Location in patent: Paragraph 0391

5
[ 1830-54-2 ]
[ 372118-01-9 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: US2004/77653,2004,A1
[4]Patent: US2019/152948,2019,A1

6
[ 83878-89-1 ]
[ 372118-01-9 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: US2004/77653,2004,A1
[4]Patent: US2019/152948,2019,A1

7
5,6-dimethoxypyridin-2-amine [ No CAS ]
[ 372118-01-9 ]
6-chloro-4-(5,6-dimethoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In acetonitrile; at 70℃; for 16h;	Step 4 6-Chloro-4-(5,6-dimethoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid methyl ester A mixture of <strong>[372118-01-9]4,6-dichloro-pyridazine-3-carboxylic acid methyl ester</strong> (1.0 g, 4.83 mmol) and 5,6-dimethoxypyridin-2-amine (968 mg, 6.28 mmol) was dissolved in acetonitrile (5 mL) and heated at 70 C. for 16 h. The mixture was concentrated in vacuo and the crude mass obtained was purified by chromatography (silica, 100-200 mesh, 10-70% ethyl acetate in hexane) to give 6-chloro-4-(5,6-dimethoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid methyl ester (830 mg, 53%) as a yellow solid. LC-MS: 325.2 [M+H]+.

Reference： [1]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 209

8
[ 372118-01-9 ]
[ 97634-83-8 ]
[ 1446819-70-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	In acetonitrile; at 130℃; for 14h;	Step 1 Methyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate A mixture of <strong>[372118-01-9]methyl 4,6-dichloropyridazine-3-carboxylate</strong> (0.69 g, 3.33 mmol) and 6-tert-butylpyridin-2-amine (1.00 g, 6.67 mmol) was dissolved in acetonitrile (3 mL) and heated at 130 C. for 14 h The dark brown mixture was cooled, concentrated onto silica, and purified by chromatography (silica, 80 g, 0-20% acetone in dichloromethane, 40 min) to give methyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (372 mg, 1.16 mmol, 35%) as a yellow solid. MS (EI/CI) m/z: 321.0 [M+H].
35%	In acetonitrile; at 130℃; for 14h;	Step 1 Methyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate A mixture of <strong>[372118-01-9]methyl 4,6-dichloropyridazine-3-carboxylate</strong> (0.69 g, 3.33 mmol) and 6-tert- butylpyridin-2-amine (1.00 g, 6.67 mmol) was dissolved in acetonitrile (3 mL) and heated at 130 C for 14 h. The dark brown mixture was cooled, concentrated onto silica, and purified by chromatography (silica, 80 g, 0 to 20 % acetone in dichloromethane, 40 min) to give methyl 4- (6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (372 mg, 1.16 mmol, 35 %) as a yellow solid. MS (EI/CI) m/z: 321.0 [M + H].

Reference： [1]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0318; 0319
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: WO2014/60371,2014,A1 .Location in patent: Page/Page column 50-51

9
[ 372118-01-9 ]
[ 1159817-43-2 ]
[ 1446792-27-3 ]

Yield	Reaction Conditions	Operation in experiment
17.5%	In acetonitrile; at 80℃; for 48h;Sealed tube;	Step 1 Methyl 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxylate A heavy walled resealable tube was charged with <strong>[372118-01-9]methyl 4,6-dichloropyridazine-3-carboxylate</strong> (1.3 g, 6.28 mmol) and 6-cyclobutylpyridin-2-amine (931 mg, 6.28 mmol) in acetonitrile (6.00 mL). The tube was heated with stirring in an oil bath at 80 C. for 48 h. Solvent was evaporated under vacuum, the residue was dissolved in dichloromethane and then purified by flash chromatography (spherical silica 20-45 muM, 50 g, Versaflash Supelco) eluting with 0 to 10% over 20 min dichloromethane/acetone to give methyl 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxylate (350 mg, 17.5% yield) as a light yellow solid. 1H NMR (CHLOROFORM-d) delta: 10.62 (s, 1H), 9.49 (s, 1H), 7.59 (t, J=7.9 Hz, 1H), 6.85 (d, J=7.6 Hz, 1H), 6.73 (d, J=8.3 Hz, 1H), 4.10 (s, 3H), 3.67 (quin, J=8.6 Hz, 1H), 2.24-2.58 (m, 4H), 1.85-2.22 (m, 2H); LC-MS 319.0 [M+H]+.

Reference： [1]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0328;0329

10
[ 372118-01-9 ]
[ 1446791-52-1 ]

Reference： [1]Patent: US2013/178478,2013,A1

11
[ 372118-01-9 ]
[ 1446791-54-3 ]

Reference： [1]Patent: US2013/178478,2013,A1

12
[ 372118-01-9 ]
[ 1446790-50-6 ]

Reference： [1]Patent: US2013/178478,2013,A1

13
[ 372118-01-9 ]
[ 1446792-09-1 ]

Reference： [1]Patent: US2013/178478,2013,A1

14
[ 372118-01-9 ]
[ 1446790-67-5 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Patent: US2013/178478,2013,A1
[3]Patent: US2013/178478,2013,A1
[4]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691

15
[ 372118-01-9 ]
[ 1446792-23-9 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: WO2014/60371,2014,A1

16
[ 372118-01-9 ]
[ 1446792-25-1 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691

17
[ 372118-01-9 ]
[ 1446790-71-1 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691

18
[ 372118-01-9 ]
[ 1446792-29-5 ]

Reference： [1]Patent: US2013/178478,2013,A1

19
[ 372118-01-9 ]
[ 1446792-31-9 ]

Reference： [1]Patent: US2013/178478,2013,A1

20
[ 372118-01-9 ]
[ 1446790-75-5 ]

Reference： [1]Patent: US2013/178478,2013,A1

21
[ 372118-01-9 ]
[ 1446792-71-7 ]

Reference： [1]Patent: US2013/178478,2013,A1

22
[ 372118-01-9 ]
[ 1446790-90-4 ]

Reference： [1]Patent: US2013/178478,2013,A1

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[ 372118-01-9 ]
[ 1446791-31-6 ]

Reference： [1]Patent: US2013/178478,2013,A1

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[ 372118-01-9 ]
[ 1446791-35-0 ]

Reference： [1]Patent: US2013/178478,2013,A1

25
[ 372118-01-9 ]
[ 1446791-41-8 ]

Reference： [1]Patent: US2013/178478,2013,A1

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Ghs Precautionary Statements

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 372118-01-9 ]

Quality Control of [ 372118-01-9 ]

Related Doc. of [ 372118-01-9 ]

Product Details of [ 372118-01-9 ]

Safety of [ 372118-01-9 ]

Application In Synthesis of [ 372118-01-9 ]

[ 372118-01-9 ] Synthesis Path-Upstream 1~3

[ 372118-01-9 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 372118-01-9 ]

Chlorides

Esters

Related Parent Nucleus of [ 372118-01-9 ]

Pyridazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 372118-01-9 ]

Related Parent Nucleus of
[ 372118-01-9 ]